Multi-step reaction with 14 steps
1.1: 90 percent / CSA / CH2Cl2 / 1.5 h / 20 °C
2.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / -78 °C
2.2: 92 percent / tetrahydrofuran / 13 h / 20 °C
3.1: 95 percent / K3PO4; PdCl2(dppf) / dimethylformamide / 3 h / 80 °C
4.1: 92 percent / Pd/C / methanol / 1.5 h / 20 °C
5.1: 72 percent / PPTS; EtOH / methanol / 3 h / 50 °C
6.1: 96 percent / CSA / CH2Cl2 / 1.5 h / 20 °C
7.1: 94 percent / LiBH4 / methanol; tetrahydrofuran / 19 h / 3 - 20 °C
8.1: lithium / tetrahydrofuran; liquid ammonia / 0.5 h / -78 °C
9.1: 5.71 g / aq. NaHCO3 / ethyl acetate / 1 h / 20 °C
10.1: 68 percent / DMAP; Et3N / tetrahydrofuran / 11 h / 20 °C
11.1: DIBAL-H / toluene; CH2Cl2 / 2 h / -78 - 20 °C
12.1: 7.57 g / pyridine / 12 h / 20 °C
13.1: 37 percent / p-TsOH monohydrate / CH2Cl2 / 1.2 h / 20 °C
14.1: tri-n-butylphosphine / tetrahydrofuran / 16 h / 20 °C
With
dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; lithium borohydride; ethanol; tributylphosphine; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; ammonia; ethyl acetate; N,N-dimethyl-formamide; toluene;
3.1: Suzuki-Miyaura coupling;
DOI:10.1021/ja034464j